Cestero joined the tennis staff as the assistant coahc in 1997. In addition to his work with the tennis team, he has served as the assistant for the Lyons squash team since 2012.

During his time at MHC, Cestero has worked with head coach Aldo Santiago, to help guide the Lyons to appearances in 14 of the last 16 NEWMAC Tennis Tournaments. Additionally, the squad has earned a playoff spot in 11 consecutive seasons, advancing to the tournament Semifinals in 2014.

Cestero has helped mentor a number of outstanding Mount Holyoke student-athletes, including a NEWMAC Player of the Year, three NEWMAC Rookies of the Year and countless All-Conference honorees.

Additional to his duties at Mount Holyoke, Cestero also serves as the head coach for the South Hadley High School varsity girls' tennis team. Since his arrival in 1997, he has guided the Tigers to six Divisional Championships, and to the Massachusetts State Finals in 2009.

Cestero also served as the head boy's volleyball coach at Central High School (1997-2000) and the assistant tennis coach at Holyoke Community College (1996-2000).

In addition to his coaching duties, Cestero has served in a number of teaching positions. Most recently, he served as a physical education teacher at New Leadership Charter School (2008-11) and the High School of Commerce in Springfield (1999-07).

Cestero also spent 26 years as an associate professor and lecturer at the University of Puerto Rico at Bayamon. During that time, he served as the Acting Chairman for the Department of Physical Education and as a student advisor. He also supervised the Human Exercise Laboratory and developed, trained and supervised the Athletic Trainer's Clinic.

Additionally, Cestero coached a number of teams at Baymon, including the varsity boys' and girls' tennis teams, along with the varsity girls' basketball and softball teams.

Cestero earned a Bachelor's Degree in Physical Education from the Inter-American University. He attained his Master's in Physical Education from New York University.